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Callahan became a quadriplegic in an auto accident at 21.[1][2] The accident happened in Callahan's car after a day of drinking. His car was being driven by a man with whom he was bar hopping.

Following his accident, he became a cartoonist, drawing by clutching a pen between both hands. His visual artistic style was simplistic and often rough, although still legible. It has been likened to that of William Steig, James Thurber, Richard Condie, and Ben Wicks.

For 27 years until his death, Callahan's work appeared in Willamette Week, whose cartoons occasionally led to boycotts and protests against the newspaper.

Callahan scoffed at the reactions of critics who labeled his work politically incorrect, while he delighted in the positive reactions he received from fans with disabilities. “My only compass for whether I’ve gone too far is the reaction I get from people in wheelchairs, or with hooks for hands,” Callahan said. “Like me, they are fed up with people who presume to speak for the disabled. All the pity and the patronizing. That’s what is truly detestable.”[3]

Two animated cartoon series have been based on Callahan's cartoons: Pelswick, a children's show on Nickelodeon; and Quads, a Canadian-Australian co-production, which retains the violence, joie de vivre, and political incorrectness of his cartoons. The main character, who "walked out of a bar and into a car," as the theme song relates, is a quadriplegic who won a large settlement from the rich driver who ran over him, and lives in a mansion with his buxom girlfriend, gay Australian physical therapist, and a cast of fellow handicapees. Their outrageous adventures infuriate the neighbours, which include an angry nun, the milquetoast millionaire who originally ran over the main character, and his domineering, Joan Riversesque wife.

Friends said Callahan realized that his cartooning was a form of counseling, which led to him pursuing a master's degree in counseling at Portland State University. However, his deteriorating health prevented him from finishing his first term.[4]

In 2005 Dutch film maker Simone de Vries made a documentary on Callahan, 'Raak me waar ik voelen kan' ('Touch me someplace I can feel').[5]

Callahan died on July 24, 2010, following surgery for chronic bed sores,[6] although his brother stated the causes of his death were complications of quadriplegia and respiratory problems.[2]

John Callahan worked on nudes and a portrait project, shown in several galleries throughout its progression.

Callahan was also a songwriter. He released his first CD in 2006. The Independent of London calls his songs "Beautiful, but dark". He wrote all the music and lyrics himself and was backed up by many notable musicians. A Dutch film crew recorded the studio sessions in which Callahan played a simplified piano version of "Roll Away The Day". The album is produced by blues musician Terry Robb, with a special cameo appearance by Tom Waits.

John Callahan was adopted as an infant, and had five siblings. At age 8, he was molested by a female teacher.[7] He began drinking at the age of fourteen. “I used the alcohol to hide the pain of the abuse,” Callahan has said. After the car accident that caused his spinal cord injury, he went through extensive rehabilitation. At the age of 27, he gave up drinking alcohol. He made his home in Portland, Oregon.[8]